2017.11.27 10:22

[Thu. 23 Nov. 2017] Prof. Sung-Gon Kim/Department of Chemistry, Kyonggi University, Suwon, Korea



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Speaker Prof. Sung-Gon Kim
Date Thu. 23 Nov. 2017
Time 5:00pm
Venue #331, Asan Hall, College of Science

 “Organocatalytic Cascade Reactions for the Asymmetric Synthesis 

of Fused-ring Compounds”



Fused-ring structural units including chroman, indoline, pyrrolidine and hydroqunoline are widely distributed in nature and many biologically active compounds. Molecules containing these structural units exhibit a broad range of bioactivities such as anticancer, antiviral, antitumar, antimicrobial, sex pheromone, and central nervous system activity. Owing to the importance of these class of compounds, the stereoselective synthesis of fused-ring compounds is a noteworthy synthetic goal. In this presentation, we demonstrate the asymmetric synthesis of hydroquinoline, hydroquinazoline, and indolines via catalytic cascade reaction.

First, A synthetic method for the construction of fully substituted enantioenriched 1,4-dihydroquinolines using an organocatalytic aza-Michael/Michael cascade reaction has been developed (Sheme 1). 1 The asymmetric reaction of 2-(tosylamino)phenyl α,β-unsaturated ketones with alkynyl aldehydes, promoted by diphenylprolinol O-TMS ether as an organocatalyst, generated chiral 1,4-dihydroquinolines in good to high yields with excellent enantioselectivities (up to  97% ee)





We have also found a concise synthetic route to valuable highly functionalized benzosulfamidate-fused tetrahydroquinazoline (Scheme 2).2 The [4+2] cycloaddition of o-N-Cbz-amino-b-nitrostyrene with benzoxathiazine 2,2-dioxide using an imidazole as the catalyst afforded tetrahydroquinazolines with high diastereoselectivities. 






In addition, we have established the synthesis of chiral benzosulfamidate-fused pyrrolidines through an Mannich/aza-Michael cascade reaction of δ-formyl-a,b-unsaturated ketones with cyclic N-sulfimines (Scheme 3).This simple domino process afforded diverse highly functionalized pyrrolidines in good yields with high diastero- and enantioselectivities.







1. Lee, Y.; Heo, S.; Kim, S.-G. Adv. Synth. Catal. 2015357, 1545-1550.

2. Sim, J.-T.; Kim, H. Kim, S.-G. Tetrahedron Lett201657, 5907-5910.

3. Kim, H.; Kim, Y.; Kim, S.-G. J. Org. Chem201782, 8179-8185.

List of Articles
No. Subject Speaker Date
Notice Spring semester 2019 Seminar Schedule file - -
65 Fall semester 2018 Seminar Schedule file - -
64 Fall semester 2016 Seminar Schedule file - -
63 Spring semester 2017 Seminar Schedule file - -
62 [Thu. 27 Apr. 2017] Seminar was canceled! - -
61 Fall semester 2017 Seminar Schedule file - -
60 [Wed. 5 July. 2017] Seminar is canceled! - -
59 7th Jilin-Korea-Waseda Alliance Annual Symposium file - August 17 ~ 19, 2017
58 [Fri. 13 Oct. 2017] Dr. J. Nathan Hohman/The Molecular Foundry, Lawrence Berkeley National Laboratory, California, USA Dr. J. Nathan Hohman Fri. 13 Oct. 2017
57 [Fri. 16 Jun. 2017] Prof. Martin Thuo/Department of Materials Science and Engineering, Iowa State University, USA Prof. Martin Thuo Fri. 16 Jun. 2017
56 [Fri. 17 Mar. 2017] 9th RINS Symposium file - Fri. 17 Mar. 2017
55 [Fri. 30 Oct. 2017] Prof. Igor Rodin/Department of Chemistry, Moscow State University, Moscow, Russia Prof. Igor Rodin Fri. 30 Oct. 201
54 [Fri. 17 Jun. 2016] Prof. Jianwei Sun/Remote Control in Brønsted Acid Catalysis: New Strategies for the Synthesis of Chiral Building Blocks and Medium Rings Prof. Jianwei Sun Friday 17 June 2016
53 [January 24, 2018] Electro-Optic Organic THz Wave Sources file Prof. O-Pil Kwon(Ajou University) January 24, 2018 (Wednesday)
52 [March 20, 2019] Challenges in molecular dynamics simulations of unfolded proteins and protein-DNA complexes file Dr. Jejoong Yoo March 20, 2019
51 [March 27, 2019] Hyperpolarization Researches with NV center, 129Xe and Parahydrogen file Prof. Keunhong Jeong March 27, 2019
50 [Mon. 16 Oct. 2017] Prof. Kirk S. Schanze/Department of Chemistry, University of Texas at San Antonio, Texas, USA Prof. Kirk S. Schanze Mon. 16 Oct. 2017
49 [Mon. 9 Jan. 2017] Prof. Sungwook Woo/Wyss Institute for Biologically Inspired Engineering, Harvard University, USA Prof. Sungwook Woo Mon. 9 Jan. 2017
48 [Mon. 13 Oct. 2016] Prof. Amir H. Hoveyda/Multicomponent Catalytic Synthesis of Organoboron Compounds for Scalable Natural Product Synthesis Prof. Amir H. Hoveyda Monday 13 October 2016
47 [November 14, 2017] Zero-Point Energy, Fluctuations, and Dissipation : A (Mostly) Quantum-Optical Perspective Prof. Milonni, Peter November 14, 2017
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